Methyl Anthranilate → N-(3',4'-dimethoxycinnamoyl)anthranilic acid

HRID 1579043노트

반응식

HRID 1579043 반응식
O1CCOCC1.[CH3:7][O:8][C:9]1[CH:10]=[C:11]([CH:17]=[CH:18][C:19]=1[O:20][CH3:21])[CH:12]=[CH:13][C:14]([OH:16])=O.P(Cl)(Cl)(Cl)=O.[C:27]([O:36]C)(=[O:35])[C:28]1[C:29](=[CH:31][CH:32]=[CH:33][CH:34]=1)[NH2:30]>N1C=CC=CC=1>[CH3:7][O:8][C:9]1[CH:10]=[C:11]([CH:17]=[CH:18][C:19]=1[O:20][CH3:21])[CH:12]=[CH:13][C:14]([NH:30][C:29]1[C:28](=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:27]([OH:36])=[O:35])=[O:16]

참가 물질

6

반응물 4

HCID 8635Methyl AnthranilateHCID 168483',4'-Dimethoxycinnamic acidHCID 24813Phosphorus oxychlorideHCID 312751,4-Dioxane

생성물 1

HCID 5527N-(3',4'-dimethoxycinnamoyl)anthranilic acid수율 63.6%

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

To a mixture of 20 ml of dry dioxane and 0.7 g of dry pyridine were added 2 g of 3,4-dimethoxycinnamic acid, 1.6 g of phosphorus oxychloride and 1.6 g of methyl anthranilate. The mixture was heated under reflux for 2 hours to effect reaction. After completion of the reaction, the reaction mixture was concentrated and the residue was dissolved with heating in ethanol and then cooled whereby crystals were precipitated. The crystals were separated by filtration and treated in a manner similar to that described in Example 5 to effect hydrolysis of the ester group. The product was recrystallized from chloroform to obtain 2 g of N-(3',4'-dimethoxycinnamoyl)-anthranilic acid having a melting point of 211°-213°C.

후처리

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 2 hours
  3. customreaction
  4. customAfter completion of the reaction
  5. concentrationthe reaction mixture was concentrated
  6. dissolutionthe residue was dissolved
  7. temperaturewith heating in ethanol
  8. temperaturecooled whereby crystals
  9. customwere precipitated
  10. customThe crystals were separated by filtration
  11. additiontreated in a manner similar to
  12. customhydrolysis of the ester group
  13. customThe product was recrystallized from chloroform

출처 및 근거

ORD 기록
ord-3bc097cbb3964bb4a5b5fd932e29f708
출처 데이터셋
uspto-grants-1976_02
특허 번호
US03940422

반응 노트

불러오는 중…